This project has two objectives. The first is the total synthesis of the antibiotic antitumor agent lavendamycin through an efficient five-step route. The proposed plan involves a Pictet-Spengler condensation of a functionalized aldehyde with methyl ester of Beta-methyltryptophan followed by dehydrogenation and hydrolysis. The aldehyde possessing the required functionalities will be prepared by a Diels-Alder condensation of a 1-azadiene system with an aminohaloquinone followed by oxidation. It should be noted that the tetrahydro derivative of the Beta-carboline portion (ring C) of this system is an intermediate in the synthetic scheme and it may also be physiologically active. The second objective of the project is to apply the Diels-Alder reactions of 1-azadienes to the synthesis of Beta-carbolines and their tetrahydro derivatives, specifically the less-known compounds possessing substitutions at position 4 of the Beta-carboline nucleus. The synthetic scheme involves an aldol type condensation of the o-nitrotoluene carbanion with an N,N-dimethylhydrazone of an Alpha-keto ester to produce the corresponding hydrazone. Silylation of the resulting keto group affords an oxygenated 1-aza-1,3-diene system. The Diels-Alder condensation of this diene with a range of acetylenic and ethylenic dienophiles followed by desilylation and Rissert condensation gives hydro carbolines which can be converted to the Beta-carbolines. Depending on the dienophile chosen, Beta-carbolines with different substituents at position 4 will be obtained.